89588-28-3

Usage

Type of compound

Purine derivative

Structure

Contains a pyrimidine ring fused to an imidazole ring

Pharmacological properties

Known for its pharmacological properties

Usage

Often used as a reagent in organic chemistry experiments

Physical appearance

White crystalline powder

Stability

Relatively stable under normal conditions

Applications

Useful in drug development and synthesis

Potential

Has potential applications in pharmaceutical research and development

Upstream product

• 172302-06-6 1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carboxylic acid amide 
• 506-68-3 bromocyane 
• 6336-13-6 8-acetoxymercuri-caffeine 
• 6937-66-2 8,8'-mercuribis-caffeine 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 151-50-8 potassium cyanide 
• 10381-82-5 8-bromocaffeine 
• 557-21-1 dicyanozinc 
• 773837-37-9 sodium cyanide 
• 5415-41-8 8-iodo-1,3,7-trimethyl-3,7-dihydro-1 H-purine-2,6-dione 

Downstream Products

• 109595-94-0 8-(1-hydroxy-2-methylamino-1-phenyl-ethyl)-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione 
• 130906-69-3 8-(2-bromo-1-hydroxy-1-phenyl-ethyl)-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione 
• 32086-89-8 8-(1-hydroxyethyl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione 

Relevant academic research and scientific papers

Electrochemical C?H Functionalization of (Hetero)Arenes—Optimized by DoE

A novel approach towards the activation of different arenes and purines including caffeine and theophylline is presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron-doped diamond (BDD) electrodes. Good yields up to 59 percent were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized using Design of Experiment (DoE) techniques giving a detailed insight to the significance of the reaction parameters. The mechanism was investigated by cyclic voltammetry (CV). Subsequent transition metal-catalyzed as well as metal-free functionalization led to interesting motifs in excellent yields up to 94 percent.

Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds

A method for regioselective cyanation of heterocycles has been developed. A number of aromatic heterocycles as well as azulene can be cyanated in reasonable to good yields by using a copper cyanide catalyst and an iodine oxidant.

Functionalization including fluorination of nitrogen-containing compounds using electrochemical oxidation

Nitrogen-containing compounds have been subjected to electrochemical oxidation with Et3N-3HF as an electrolyte. Caffeine afforded 8- fluorocaffeine as a sole product in 40.3% yield. Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 17.5 and 4.6% yields, respectively. Similar electrochemical oxidation of caffeine with methanol, KCl, or KCN afforded 8-methoxycaffeine, 8-chlorocaffeine, or 8- cyanocaffeine, respectively.

Synthesis of purinecarbonitriles by Pd(0)-catalysed coupling of halopurines with zinc cyanide

Pd(0)-catalysed coupling of halopurines with zinc cyanide allows the smooth introduction of the cyano group into the purine 2-, 6- and 8-positions. Pronounced ligand effects were observed, and tetrakis(tri-2-furylphosphine)palladium(0) was found to be the

Functionalization Including Fluorination of Caffeine, Guanosine Tetraacetate, and Uridine Triacetate using Electrochemical Oxidation

The title compounds have been subjected to electrochemical oxidation with Et3N-3HF as an electrolyte.Caffeine afforded 8-fluorocaffeine as a sole product in 43percent yield.Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 7.3 and 4.8 percent yield, respectively.Similar electrochemical oxidation of caffeine with methanol, KCl or KCN yielded 8-methoxycaffeine, 8-chlorocaffeine, or 8-cyanocaffeine, respecticvely.

SOME NEW HALO- AND CYANO-DEMERCURATION REACTIONS OF 8-ACETOXYMERCURI- AND 8,8'-MERCURIBIS-CAFFEINES

On acting upon 8-acetoxymercuri-caffeine (1) and/or 8,8'-mercuribis-caffeine (2) with aqueous solutions of KI3, KBr3, ICN, BrCN or with an excess of neat liquid SO2Cl2, SCl2, S2Cl2, and SF4, the following 8-X-substituted caffeines, X=CN (3), I (4), Br (5), Cl (6), and F (7), were prepared, sometimes in excellent yields.Seven of these methods of demercuration of organomercurials have not been reported so far in the literature.